e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron

Synthesis and reactivity of lithium tri (quinolinyl) magnesates

S Dumouchel, F Mongin, F Trécourt, G Quéguiner

Index: Dumouchel, Sylvain; Mongin, Florence; Trecourt, Francois; Queguiner, Guy Tetrahedron, 2003 , vol. 59, # 43 p. 8629 - 8640

Full Text: HTML

Citation Number: 56

Abstract

2-, 3-and 4-Bromoquinolines were converted to the corresponding lithium tri (quinolinyl) magnesates at− 10° C when exposed to Bu3MgLi in THF. The resulting organomagnesium derivatives were quenched with various electrophiles or involved in metal-catalyzed coupling reactions with heteroaryl halides to afford functionalized quinolines.

2-Bromoquinoline Structure

2-Bromoquinoline

Diphenyl disulfide Structure

Diphenyl disulfide

~15%

2-(PHENYLTHIO)QUINOLINE Structure

2-(PHENYLTHIO)Q...

4-Bromoquinoline Structure

4-Bromoquinoline

~56%

4-Iodoisoquinoline Structure

4-Iodoisoquinoline

3-Bromothiophene Structure

3-Bromothiophene

3-Bromoquinoline Structure

3-Bromoquinoline

~15%

3-(3-Thienyl)quinoline Structure

3-(3-Thienyl)qu...

2-Bromoquinoline Structure

2-Bromoquinoline

Benzaldehyde Structure

~40%

2-Quinolinemethanol, a-phenyl- Structure

2-Quinolinemeth...

1-Bromoisoquinoline Structure

1-Bromoisoquinoline

Bromobenzene Structure

~23%

Phenylisoquinoline Structure

Phenylisoquinoline

3-Bromoquinoline Structure

3-Bromoquinoline

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~72%

3-Quinolinecarboxaldehyde Structure

3-Quinolinecarb...

2-Bromopyridine Structure

2-Bromopyridine

2-Bromoquinoline Structure

2-Bromoquinoline

~28%

2-pyridin-2-ylquinoline-4-carboxylic acid Structure

2-pyridin-2-ylq...

Carbon dioxide Structure

4-Bromoquinoline Structure

4-Bromoquinoline

~38%

4-Quinolinecarboxylic acid Structure

4-Quinolinecarb...

3-Bromoquinoline Structure

3-Bromoquinoline

Bromobenzene Structure

~30%

Quinoline, 3-phenyl- Structure

Quinoline, 3-phenyl-

3-Bromoquinoline Structure

3-Bromoquinoline

Iodobenzene Structure

~28%

Quinoline, 3-phenyl- Structure

Quinoline, 3-phenyl-

2,5-Dibromopyridine Structure

2,5-Dibromopyridine

3-Bromoquinoline Structure

3-Bromoquinoline

~54%

3-(5-bromopyridin-2-yl)quinoline Structure

3-(5-bromopyrid...

3-Bromoquinoline Structure

3-Bromoquinoline

Carbon dioxide Structure

~46%

Quinoline-3-carboxylic acid Structure

Quinoline-3-car...

2-Bromoquinoline Structure

2-Bromoquinoline

~49%

Quinoline, 2-iodo- Structure

Quinoline, 2-iodo-

2-Bromoquinoline Structure

2-Bromoquinoline

3-Bromoquinoline Structure

3-Bromoquinoline

~49%

2-quinolin-3-ylquinoline Structure

2-quinolin-3-yl...

Nucleophile and aryl radical reactivity in SRN1 aromatic nuc...

[Amatore, Christian; Oturan, Mehmet A.; Pinson, Jean; Saveant, Jean-Michel; Thiebault, Andre Journal of the American Chemical Society, 1985 , vol. 107, p. 3451 - 3459]

Nucleophile and aryl radical reactivity in SRN1 aromatic nuc...

[Amatore, Christian; Oturan, Mehmet A.; Pinson, Jean; Saveant, Jean-Michel; Thiebault, Andre Journal of the American Chemical Society, 1985 , vol. 107, p. 3451 - 3459]